Sodium hydride → HCID 73655563, compound

HRID 1607836Notes

Reaction equation

HRID 1607836 reaction equation
[OH:1][N:2]=[C:3]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:15](=[O:16])[CH2:14][NH:13][C:12]2=[O:17])=[CH:7][CH:6]=1)[CH3:4].[H-].[Na+].[H][H].[CH2:22](Br)[CH:23]=[CH:24][CH3:25]>C(OCC)C.O>[CH2:22]([O:1][N:2]=[C:3]([C:5]1[CH:6]=[CH:7][C:8]([N:11]2[C:15](=[O:16])[CH2:14][NH:13][C:12]2=[O:17])=[CH:9][CH:10]=1)[CH3:4])[CH:23]=[CH:24][CH3:25]

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 1224142-Butene, 1-bromo-HCID 85544988HCID 85544988, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 73655563HCID 73655563, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of 0.01 mol of 3-[4-(1-hydroxyiminoethyl)phenyl]hydantoin in diethyl ether is treated with 0.01 mol of sodium hydride. After hydrogen evolution stops, 0.011 mol of crotyl bromide is added. The reaction mixture is stirred for 2 hours. The reaction mixture is then poured into cold water, the layers are separated, and the aqueous layer is extracted with diethyl ether. The combined ether solutions are dried over MgSO4and filtered, and the solvent is removed by rotary evaporator to yield 3-[4-(1-crotyloxyiminoethyl)phenyl]hydantoin.

Workup

  1. customthe layers are separated
  2. extractionthe aqueous layer is extracted with diethyl ether
  3. dry with materialThe combined ether solutions are dried over MgSO4and
  4. filtrationfiltered
  5. customthe solvent is removed by rotary evaporator

Sources & evidence

ORD record
ord-5fdaec4a42bd420496da608deef49c4e
Source dataset
uspto-grants-1989_09
Patent number
US04868061

Reaction notes

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